Download PDF
Synthesis 2009(11): 1829-1833  
DOI: 10.1055/s-0028-1088063
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Reactions of Morita-Baylis-Hillman Acetates with Huisgen Zwitterions: A Novel Strategy for the Synthesis of β-Amino Acid Derivatives

Anu Josea, Rony Rajan Paula, Resmi Mohana, Smitha C. Mathewa, A. T. Bijua, Eringathodi Sureshb, Vijay Nair*a
a Organic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India
Fax: +91(471)2491712; e-Mail: vijaynair_2001@yahoo.com;
b Analytical Science Discipline, Central Salt and Marine Chemicals Research Institute, Bhavanagar 364002, India
Further Information

Publication History

Received 16 January 2009
Publication Date:
27 April 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

The reaction of Huisgen Zwitterion with Morita-Baylis-Hillman acetates afforded β-amino acid derivatives.

Key words

Huisgen zwitterion - Morita-Baylis-Hillman acetate - β-amino acid

    References

  • 1 Huisgen R. In The Adventure Playground of Mechanisms and Novel Reactions: Profiles, Pathways and Dreams   Seeman JI. American Chemical Society; Washington DC: 1994.  p.62 
    Google Scholar
  • 2 Mitsunobu O. Eguchi M. Bull. Chem. Soc. Jpn.  1971,  44:  4145 
    Google Scholar
  • 3a Nair V. Rajesh C. Vinod AU. Bindu S. Sreekanth AR. Mathen JS. Balagopal L. Acc. Chem. Res.  2003,  36:  899 
    Google Scholar
  • 3b Nair V. Menon RS. Sreekanth AR. Abhilash N. Biju AT. Acc. Chem. Res.  2006,  39:  520 
    Google Scholar
  • 4 Nair V. Biju AT. Mathew SC. Babu PB. Chem. Asian J.  2008,  3:  810 
    CrossrefGoogle Scholar
  • 5 Nair V. Mathew SC. Biju AT. Suresh E. Angew. Chem. Int. Ed.  2007,  46:  2070 
    CrossrefGoogle Scholar
  • 6 Nair V. Biju AT. Vinod AU. Suresh E. Org. Lett.  2005,  7:  5139 
    CrossrefGoogle Scholar
  • For excellent reviews on MBH reactions, see:
  • 7a Basavaiah D. Rao J. Satyanarayana T. Chem. Rev.  2003,  103:  811 
    Google Scholar
  • 7b Basavaiah D. Rao KV. Reddy RJ. Chem. Rev.  2007,  36:  1581 
    Google Scholar
  • 7c Singh V. Batra S. Tetrahedron  2008,  64:  4511 
    Google Scholar
  • For selected examples of the reactivity of nucleophiles towards MBH adducts, see:
  • 8a Basavaiah D. Rao JS. Reddy RJ. J. Org. Chem.  2004,  69:  7379 
    Google Scholar
  • 8b Basavaiah D. Sharada DS. Kumaragurubaran N. Mallikarjuna Reddy R. J. Org. Chem.  2002,  67:  7135 
    Google Scholar
  • 8c Kim SC. Gowrisankar S. Kim JN. Tetrahedron Lett.  2006,  47:  3463 
    Google Scholar
  • 8d Das B. Chowdhury N. Damodar K. Benerjee J. Chem. Pharm. Bull.  2007,  55:  1274 
    Google Scholar
  • 8e Jiang YQ. Shi LY. Shi M. J. Am. Chem. Soc.  2008,  130:  7202 
    Google Scholar